Now I'm really intrigued by what it takes to get "freelance interim CTO" jobs - and whether this is with tiny one-person shops (where the CTO is also "the developer"), middle-size businesses (10-50), or enterprises that lost an executive to poaching or illness and need someone to plug the gap until their headhunter's got a new one lined up.
Right now, it's mid size businesses with 50-75 FTE product development departments, but when I will be 50+, I want to get also projects at bigger companies :)
What was the hardest hurdle to take when making the transition?
The switch to freelancing also sort of came naturally - a permanent job stopped very abrupt, and a headhunter that helped me find developers before approached me with the idea, because he had a customer who needed help.
I guess you also have to be "management material". Either you can do it or not. To a certain degree, you can learn management stuff, but honestly you have to be that kind of person.
Jus out of curiosity, what exactly do you mean by that kind of person.
Now since about four years, I'm a freelance interim CTO and help companies that struggle inside and around the product development department.